Making the Ask: The Most Human Moment in Major Gifts
Why practice—and discomfort—are your best fundraising tools
There’s a moment in every major gift journey where strategy meets vulnerability.
It’s the ask.
No matter how long you’ve been cultivating a donor, how well you’ve mapped their passions to your mission, or how confident you are in your cause—there’s always a flicker of nerves before you ask for a significant gift.
That’s because major gift fundraising isn’t transactional. It’s deeply human.
The Ask Isn’t a Performance—It’s a Conversation
Too often, fundraisers treat “the ask” like a scene they have to nail in one take.
But the truth is, it’s not a pitch. It’s a partnership-building moment.
The most successful major gift solicitations are grounded in trust, mutual understanding, and a clear invitation—not pressure.
Your goal isn’t to impress.
It’s to connect.
To invite.
To co-create a vision for impact, together.
Objections Aren’t Rejections
One of the biggest myths in major gifts is that objections = failure.
In reality, objections are progress. They mean the donor is thinking critically. They’re engaging. They care enough to voice a concern rather than silently disengage.
Whether it’s:
“I’m not ready to commit at that level.”
“I need to talk to my partner.”
“We’re prioritizing a different issue this year.”
…your job is to listen, stay curious, and keep the relationship open—not shut down.
Why You Must Practice the Ask
If you’re waiting to feel fully confident before you ask, you’ll wait forever.
The only way to build confidence is to practice. Not just writing out what you’d say—but saying it out loud, with a coach or colleague, and inviting feedback.
Practice helps you:
Get comfortable hearing yourself speak the ask
Stay steady when a donor surprises you
Hear your tone, pacing, and language clearly
Normalize objections so you’re not rattled when they arise
What I Recommend to Fundraisers
Whether you’re new to major gifts or a seasoned pro, here are three things you can start doing now:
Script the invitation (not the conversation)
Prepare a clear, confident invitation to give—but leave room for dialogue.Role-play the objection you fear most
What’s the “worst-case” response you dread? Practice hearing it and staying grounded.Debrief every ask
Whether the answer is yes, no, or maybe—reflect on what went well and what you’d adjust. Every ask makes the next one stronger.
Fundraising Is a Skill—Not a Trait
You don’t have to be extroverted. You don’t have to be perfect.
You just have to show up prepared, practiced, and open to learning.
Major gift fundraising isn’t about having all the answers. It’s about building trust, navigating complexity, and staying in relationship—even when things get uncertain.
So don’t avoid the ask.
Prepare for it.
Practice it.
And when the time comes—make it with heart.
Want help practicing your next ask—or working through a donor scenario you’re unsure how to navigate? I offer coaching for fundraisers and teams who want to strengthen their major gift strategy, confidence, and conversations.
